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THC extraction w/ citric acid?


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#1 lechuck12

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Posted 17 April 2011 - 10:09 AM

hello friends,

i stumbled over ths recipe for thc infused iced tea, it uses citric acid to extract the thc from trim/bud

http://forum.grassci...cipe-guide.html

im just wondering if this works, since I never read about using citric acid as solvent for thc before.. but the author seems to know what hes talking about so what do you guys think?

#2 Shadowlord

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Posted 17 April 2011 - 10:19 AM

I don't know.
Doesn't sound right but then I am not a chemist.
Be nice if it is a sound method as I don't always like baking and don't drink alcohol so green dragon is out.
Be a great way to beat the summer heat and suck down some Iced Weed Teas. A real green tea for you!

#3 Phineas_Carmichael

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Posted 17 April 2011 - 10:41 AM

Doesn't sound right but then I am not a chemist.

Neither is the original author... :mistrust: Check these words concerning the invariable Grass City "I thought you had to heat THC to make it active" argument:

Slight heat however can be beneficial since some THC can become a volatile vapor and be absorbed into the sinuses and produce a quicker effect, but the heat is not absolutely necessary for THC to be active.

Or this little gem :weedpoke:

If you eat a nug of weed you will feel the effects with no added heat, this is because of acid.

THC's boiling point is 157*C, a temp that his aqueous THC extract can never physically reach, and eating a nug of weed won't get you anything but a stomachache. It's possible that he's converting thc into water soluble thc-citrate, but I highly doubt it. I call placebo on this one but I've been proven wrong before...

#4 Kioshoa

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Posted 19 April 2011 - 12:10 PM

Well, Phin, I don't know about the acid, but I've eaten sacks before and been completely altered, no heat added. As I understand it, some of the THC is decarboxylated(sp?) without the aid of heat. Not effecient, but still kind of viable, right?

#5 Phineas_Carmichael

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Posted 19 April 2011 - 12:28 PM

Decarboxylation has little to do with it. Breaking that carboxyl group off (turning THCA into THC) means that your buds have more orally active compound by weight than had you not decarboxylated. When you smoke it, the heat of the lighter does this.

But THC simply cannot enter the bloodstream through the digestive tract unless it is bonded to a fatty acid or an alcohol functional group as far as I understand. I'm kind of treading in speculative waters here... Maybe some of the awesome ganja cooks we have round these parts will weigh in...

My hypothesis as to why "eating sacks" got you high: There was enough fat in your stomach already (from your most previous meal) that the thc was able to bond in vivo and enter the bloodstream.
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#6 Defiance

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Posted 19 April 2011 - 12:31 PM

Cannabinoids ain't alkaloids, they're phenols and they form esters not salts. Be pretty surprised if that citric acid worked.

The only way I know to make THC water soluble is through the formation of a succinic acid ester, THC hemisuccinate. Patents are available for the Curious.

Heat increases overall potency through decarboxylation for sure.

Edit:

...
My hypothesis as to why "eating sacks" got you high: There was enough fat in your stomach already (from your most previous meal) that the thc was able to bond in vivo and enter the bloodstream.


:thumbup:
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#7 Kioshoa

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Posted 19 April 2011 - 12:37 PM

Hmmm. That may be very possible. You know a lot more than I do, Dude. Hahaa

#8 director of sound

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Posted 19 April 2011 - 02:48 PM

yea defiance hit the nail on the head, the only known esters ate the one mentioned and the proponic acid ester as well as the acetic acid ester. all 3 involve the use hard to get acid anhydrides and in the case of the proponic acid ester needing proponic anhydride which is a scedualed substance used in the manufacture of fetanyl and PCP....:thumbdown: though under extreme dehydrative conditions using PURE THC (boil BHO oil in H2SO4 to get this) one would simply react the THC with the acid to get the ester. the use of a dehydration agent like fuming sulfuric acid or SO3, oxalyl or thionyl chloride is a must if you can only get glacial acetic acid. though this is an up and coming endevor of mine i dont havve time to work on the project yet but posts will come soon. also these THC esters not only are many times more potent than THC by weight, they are also psychedelic....:headbang:
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#9 Defiance

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Posted 19 April 2011 - 03:29 PM

using PURE THC (boil BHO oil in H2SO4 to get this)


What happens to all of the other cannabinoids?

#10 Phineas_Carmichael

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Posted 19 April 2011 - 03:38 PM

What happens to all of the other cannabinoids?

They are isomerized into Δ-9-THC aren't they?

#11 Defiance

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Posted 19 April 2011 - 04:05 PM

Well I Wonder.

I've been reading some and it makes sense to me that only other THC isomers would become delta-9 in an acid catalyzed isomerization.

That is, delta-6 can become delta-9, but cannibidiol isn't transformed.
Edit: Here's some reading on it And now I'm not even so sure delta-6 would become delta-9. Um. More reading.

I knew a guy once who ran BHO through a flash column and swore it was the only way to isolate THC isomers from the crude extract.

I didn't know there were so few esters around. I would have thought that THC would form an ester with sulfuric acid, but I guess I don't know much about ester formation anyway.

Edited by Defiance, 19 April 2011 - 04:27 PM.


#12 Defiance

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Posted 20 April 2011 - 12:17 AM

I don't see how an acid catalyzed isomerization could change an entire class of compounds into one specific isomer of one specific compound in a single step.

I think that CBD and CBN would be present after isomerization, although it's possible that CBD/CBN both exist as a collection of isomers that would be converted to one specific isomer too. No guarantees it's an active one either.

I don't think delta-6 THC is converted to any isomer of delta-9 THC because I don't see how a strong acid could change the position of the delta bond. I don't understand delta bonds very well though.

I really think the only things converted to the active trans, levo isomer of delta-9 THC during isomerization are the three other delta-9 THC isomers. And possibly the delta-6 isomers if I'm Ignorant.

Please, anyone and everyone, tell me why I'm wrong.

I also think Phin's pretty cool because he knows how to put in a little delta sign, but good luck refuting that.

Edited by Defiance, 20 April 2011 - 12:42 AM.


#13 lechuck12

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Posted 20 April 2011 - 05:50 AM

thx for all the replies guys, would have been too cool it that actually worked
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#14 Shadowlord

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Posted 20 April 2011 - 09:27 AM

I also think Phin's pretty cool because he knows how to put in a little delta sign, but good luck refuting that.


If he's doing it w/ Windows, then he's only kind of cool. :lol:

Now if he's running linux and typing them in then he's cool. I sure as hell can't figure it out and I am using the answers I've found on the web!

#15 Defiance

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Posted 20 April 2011 - 09:55 AM

I don't see how an acid catalyzed isomerization could change an entire class of compounds into one specific isomer of one specific compound in a single step.


Possibly wrong.

I think that CBD and CBN would be present after isomerization, although it's possible that CBD/CBN both exist as a collection of isomers that would be converted to one specific isomer too. No guarantees it's an active one either.


Wrong for cannibidiol at least. It's cyclized to delta-9 THC (The link uses the notation Shulgin mentioned, delta-1, but it's the same thing)

#16 Shadowlord

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Posted 20 April 2011 - 10:04 AM

Nice site in your link Defiance.

Too bad they want $42 for the PDF .

I was interested. But not that interested. :lol:
:eusa_thin

#17 Defiance

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Posted 20 April 2011 - 12:47 PM

:thumbup:

Pretty much what that link is telling me is that when we talk about isomerization we're really talking about a collection of different reactions of which isomerization is only one. They all happen to take place under reflux in a strong acid.

Cannabidiol is cyclized to one or more THC isomers (or maybe to intermediate cannabinol?) Cannabinol must be able to bond with the acidic hydrogen ions floating around to end up with the extra 4 hydrogens it needs to become one or more isomers of THC.

And finally inactive isomers of delta-9 THC are isomerized to the trans, levo isomer. This is the only step that's truly isomerization, right?

I still don't understand delta bonds and whether or not they move though.

All this Wondering is a case of me taking the term isomerization too literally I think. Sure, isomerization happens, but it happens along with Bunches of other important stuff too. It's just easier to refer to all of it by one name.

Edited by Defiance, 20 April 2011 - 12:57 PM.


#18 director of sound

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Posted 20 April 2011 - 03:22 PM

from what i read when you reflux the BHO in toluene and H2SO4 (i belive it has to be 80%+) most of the inactive isomers and cannabinoids are isomerized into active forms, it also allows the breakdown of junk terpenes and waxes present. following a few hours of reflux you would wash the toluene with first a basic solution then a plain water solution before evaping the toluene or distilling the THC to obtain a off white oil that is pure active cannabinoids. this you would use as feed stock when making the esters by dissolving it in a dry semi polar solvent like DCM or toluene and adding about 10ml/1g(cbn's) of your acid anhydride. i am insure how long the rxn takes but in a normal acid catalyzed esterification (fischer) of an aromatic component it is preformed at room temp for about 2hr employing a lewis acid catalyst usually zinc dichloride, boron trifluoride or an aluminum halide in the amount of a few hundred mg. also with microwave stimulation and no lewis acid in as little as 190 sec. but i dont think it would be too safe to put a few hundred ml of DCM and an acid anhydride in a home microwave, now if you had one of those several thousand dollar lab synth microwaves that is built for the purpose, go for it. i am un certain but the THC-ester may now be water soluable and could be separated that way but removal of the solvent may be better. it may be a little complicated to remove the lewis acid because both it and the THC-ester could be water soluable...
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#19 Defiance

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Posted 21 April 2011 - 06:48 PM

Okay I think I've got myself as straightened out about this as I can get. I still don't understand delta bonds but I guess I'll post an update if I ever do.

The 4 isomers of delta-9 THC all become a single isomer, the active one.

delta-6 THC is probably isomerized but I don't know if isomerization changes the delta bond location. I think it probably remains inactive.

CBD (cannabidiol) is cyclized into a mix of delta-6 (inactive) and delta-9 THC and is then isomerized. My question about whether or not it forms CBN is a Stupid one, it does not.

CBN (cannabinol) doesn't do much of anything. It remains 4 hydrogen ions short of becoming THC. It could maybe be hydrogenated in the presence of a catalyst into THC but I have No Idea.

But none of that seems to matter much anyway, since DoS says the THC can be distilled off. Any special precautions? Probably a short jacketed vigreux would be nice. Maybe vacuum? bp should be around 200C.

Edit: and just in case my ramblings didn't confuse enough people, isomerization is the correct term for all of this. CBD is a structural isomer of THC so cyclization is just a description of the type of isomerization that occurs in this instance. Although two different types of isomerization do occur.

Edited by Defiance, 21 April 2011 - 07:26 PM.

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#20 director of sound

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Posted 21 April 2011 - 08:02 PM

you also want to run hot (or at least very warm) water through the condenser if you are going to use a vigrux. id suggest a fredrich on top of a vigrux that has water of atleast 125*F running through it and wrap glass wool around the fredrich. if the condensers are too cold the THC will gum up and become thick making a non polar wash of the condenser necessary to recover the THC (still may be needed). a graham would be a bad idea due to the viscosity of the THC it could clog up the coil and build pressure in the setup making a dangerous situation... a slower distillation would be better than a fast one unless you have extremely efficient condensers. a slow reflux/simmer on a oil bath should do the trick. remember any residual toluene will come over first followed by some terpenes. the THC its self should start to come over at around 300*F (per "Cannabis and Cannabis Extracts: Greater Than the Sum of Their Parts? by hawthorn press THC's boiling point is 157 °C / 315 °F) vacuum distillation wouldnt be a bad idea if you have the gear but i could not tell you the temp it might come over at, you would just have to fractionally distill the oil and test out the components to find the THC but it should be one of the last to come over.
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